The Crazy Ones is a show that focuses on his relationship with his employees and his daughter but it also heavily focuses on the man’s desire to be remembered and his fear that he will slip into anonymity once he is gone from the advertising world and the world in general. It’s a universal human fear, to be honest. We all have this desire within us to be remembered. We want to do something that puts us on the map. So we work hard and we strive to be noticed by our bosses or our peers or Internet strangers. We want to feel like our lives are significant and that we make an actual, tangible difference in the world. No one at Lewis, Roberts + Roberts understands this feeling more than Simon who spends most of “Sixteen-Inch Softball” weighed down with concern over whether or not he will remain a legendary figure to his staff. Elsewhere in the episode, Sydney spends most of her time trying to buddy up to Nancy, Andrew’s girlfriend, who hates her. The younger Roberts is nothing if not persistent, but continues to fail and Andrew dissuades her from pursuing a friendship with Nancy (the reasoning for which we learn near the episode’s end).

So if you’re ready, let’s discuss more of “Sixteen-Inch Softball” and its plot as well as some character development and insights, shall we?

It’s a delightful time to be an employee of Lewis, Roberts + Roberts because our favorite ragtag group of advertising employees is chatting at the beginning of the episode, Sydney having excitedly just finished writing the company’s newsletter (which Lauren horrifyingly realized she actually READ). There’s a story that Sydney prints in the newsletter and it’s a story she prints in there every year: the story of how her father won the integral baseball game. Simon is lovingly heckled by his associates to recount the tale, which he does with great pride. Take note of the fact that “Sixteen-Inch Softball” centers around Simon’s desire to not just be the focus of everyone’s attention but to be heralded as a great for generations to come. This is what he wants his legacy to be. He wants people to continue to tell that story of him for years to come, even when we learn later on that it isn’t entirely true. We want glory; we want to be remembered and Simon is no different. But Simon admits to the group that he’s retired from softball and won’t be joining the team as they take on the accounting department in their annual game. Simon is a legend and he wants to remain that way with people adoring him, cheering for him, and recounting his tales for years to come.

But there’s a problem. Well, there are a few problems. The first is this: Simon needs to fire someone from his staff. The company has a few monetary issues and those can be absolved by simply laying off a member of his team. But Simon – avoider of conflict – doesn’t want to do that; how can he possibly be forced to ax one of his own? Instead, Gordon Lewis and he propose a deal: the normally low-ish stakes annual softball game will now hold higher stakes than ever before: the loser has to fire a member of his team.

Elsewhere in the episode, Sydney’s makes an attempt to bond with Andrew’s girlfriend Nancy. There’s only one problem: Sydney discovers that Nancy hates her. And the reason why Nancy hates her is pretty simple. You see, when Andrew and Sydney shared their kiss in “Breakfast Burrito Club,” Andrew may or may not have told Nancy that Sydney was the one to initiate the kiss. It was a lie, obviously, as Andrew was the one to initiate but Sydney – to her credit – agrees to the lie. Let’s think about this though for a moment. Sydney Roberts agrees to look like the villain just for the opportunity for someone else – someone important to a person she cares about – to like her. She’s a type-A personality and we type A people really REALLY want to be liked by everyone. Sydney can’t stand the thought of someone, anyone, being mad at her so she’s actually willing to lie in order to ensure that doesn’t happen. (It still does happen but we’ll get there in a bit.)

Meanwhile, Zach and Simon are reviewing their strategy for the softball game when Zach admits that people were hesitant to sign up for the team, knowing that they could be the reason someone from the office gets fired. Zach then has a brilliant idea: it would inspire and motivate the employees if Simon signed up to play. The man is bashful (weirdly so because Simon is never bashful) and explains that his sports-playing days are behind him. But it’s very quickly thereafter that Zach learns the true reason why Simon is reluctant to play: that amazing, game-winning pitch that he hit in his last softball game? It was a fluke. Simon was under heavy medication and accidentally made himself a legend. And now, no one can know that he’s actually really terrible at softball. Zach, blessedly, decides that he’s going to coach Simon so that he’s both confident and ready for the softball game and can play without anyone knowing his secret.

That… doesn’t go very well. Despite Zach’s best efforts, Simon is really pretty horrible at softball and there’s no way to fake it and make it at the game. When all of Zach’s logical approaches fail, he comes up with another solution: Simon’s ego. If Simon just remains confident and stands as a beacon for the team, everything will be okay. His presence will give people the confidence to do well and it won’t matter that he’s actually a horrible softball player. (It won’t hurt that Gordon will walk Simon at the game, either.) What I loved about the Zach/Simon story was that these two individuals really understand each other, perhaps better than any other pairing on the series. Zach is passionate and slightly egotistical but he has a good, genuine heart just like Simon. Simon admits to wanting the glory and the name for himself later in the episode, but during training all he wants is to not let his team – metaphorically and literally – down. Zach understands that. He knows what it feels like to want the fame and the recognition and he understands why Simon MUST be there for the people who work for him. While both characters may be self-centered at times, they really want to better themselves and the people around them. They care deeply about how others view them, to be quite honest, and that desire manifests itself in how they approach certain situations.

Armed with false confidence, the gang plays ball and the creative team is actually doing quite well. Whenever Simon gets up to bat, Gordon walks him and the other creative employees are scoring runs and sliding into home plate. But all of this changes the moment Sydney heckles Gordon for not throwing any real pitches and the accounting head decides to be a bit tougher on his colleague. Simon freaks out, confronts Zach about it (this is where he admits to wanting the entire game to be about him: he doesn’t want to look bad in front of his employees for morale reasons, sure, because he wants them to not lose hope that they can win BUT Simon also just really, really wants to be adored) and then actually manages to injure himself while batting. He insists that he is fine after being put on pain medication and it looks like everything will work itself out, right? Now that Simon is hopped up on drugs, it’ll be just like his glory story: he’ll swing, hit the pitch, send it flying over the fence and be heralded a hero by everyone at the game. And that DOES happen.

Unfortunately, it all happens within Simon’s mind. He doesn’t even hit the ball in reality, leaving the rest of the creative team (and all of the accounting team as well) baffled by Simon who legitimately believes he’s scored a home run and is running around the bases. The following day, Gordon approaches Simon and admits that it isn’t fair for him to have to fire a member of his team. He was hopped up on pain medication at the game and really who could have played well in a game when they’re under the influence anyway? (Wink wink, nudge nudge.) And so, Simon and Gordon agree to find another mature way to settle the debate of who gets fired: jousting!

If you were to extract a moral of “Sixteen-Inch Softball,” I think it would be this: it’s okay to want to be adored, to want to be loved, and to want to be remembered. That’s a completely universal human desire. But the episode is also a cautionary tale: you don’t always get remembered for the things you assume you will; you may not be remembered for your softball glory, but perhaps you’ll be remembered for that time you got up to bat – literally – for your employees. And maybe, just maybe, that’s okay.

And now, some added bonuses:

I had some feelings when Andrew admitted that looking at Nancy next to Sydney was confusing for him.

“Butter, sugar, suppressed rage of a directionless life.”

“Where are you, lost lady?”

“How can I lie to that face? You’re like a baby who shaves.”

“What do we want?” “A NEW MICROWAVE!” “ONE WITH A POPCORN BUTTON!”

“What are the chances it’ll all come back to me the second I step up to the plate?” “Ehhhh, like 95%.”

“Is it selfish that I want to make this all about me?” “That’s the very definition of selfish.”

Thanks so much for reading this (belated) review. Have a great week, y’all! :)